CN104672095B - A kind of acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two and preparation method thereof - Google Patents
A kind of acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two and preparation method thereof Download PDFInfo
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- CN104672095B CN104672095B CN201310603807.XA CN201310603807A CN104672095B CN 104672095 B CN104672095 B CN 104672095B CN 201310603807 A CN201310603807 A CN 201310603807A CN 104672095 B CN104672095 B CN 104672095B
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- ethylene diamine
- dodecane
- tetrahydroxyethyl
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Abstract
The invention discloses a kind of acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two and preparation method thereof, it is characterized in that：Using a small amount of water as solvent, n-dodecane dicarboxylic acids carries out neutralization reaction with tetrahydroxyethyl-ethylene diamine, the solution of n-dodecane dicarboxylic acids tetrahydroxyethyl-ethylene diamine salt is generated, under catalyst action, then using toluene as water entrainer, carry out refuxing esterification reaction, it is evaporated under reduced pressure and removes toluene, sebacate ethoxy tertiary amine compound is made, synthetic is a kind of acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two, with multiple groups combined with metal, preferable anti-rust action can be played；With multiple ethoxys, good water solubility；Synthetic is a kind of dibasic acid esters, has lubricity.
Description
Technical field
The present invention relates to rust-inhibiting additive synthesis technical field, espespecially a kind of acid esters multi-hydroxy ethyl ethylenediamine of n-dodecane two
Compound and preparation method thereof.
Background technology
Rust-inhibiting additive is the important component of water-based metal working fluid, with organic rust preventing additive exploitation and should
With inorganic salts rust-inhibiting additive is gradually substituted, and carboxyl is the essential groups that natural organic ligand is combined with metal.Antirust adds
Agent is added to play a part of preventing from corroding in process of metal working, the polar group in rust-inhibiting additive molecule can be adsorbed in metal
Surface, and hydrophobic alkyl forms diaphragm in metal surface, plays rust-proof effect, dissolubility and alkane of the organic molecule in water
The hydrophilic radical of base chain is relevant, not only to there is the polarity for playing anti-rust action as water miscible rust-inhibiting additive, in molecule
Group, and to have certain water solubility.With the continuous improvement of modern machinery and equipment performance, environmental requirement is increasingly harsh, raw
High performance rust-inhibiting additive is needed to use in production, life.
The content of the invention
It is an object of the invention to provide a kind of acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two and its preparation side
Method.
The present invention technical solution be：Using a small amount of water as solvent, n-dodecane dicarboxylic acids and tetrahydroxyethyl-ethylene diamine
Neutralization reaction is carried out, the solution of n-dodecane dicarboxylic acids tetrahydroxyethyl-ethylene diamine salt is generated, under catalyst action, then with toluene
For water entrainer, refuxing esterification reaction is carried out, is evaporated under reduced pressure and removes toluene, sebacate ethoxy tertiary amine compound is made, specifically
Comprise the steps of：
1) is using a small amount of water as solvent, n-dodecane dicarboxylic acids（Ⅰ）With tetrahydroxyethyl-ethylene diamine（Ⅱ）, in 50 DEG C~60 DEG C
Lower stirring reaction 1~2 hour, produce n-dodecane dicarboxylic acids tetrahydroxyethyl-ethylene diamine salt（Ⅲ）Solution, its primary chemical is anti-
It should be：
2) is using dimethylbenzene as water entrainer, under catalyst action, n-dodecane dicarboxylic acids tetrahydroxyethyl-ethylene diamine salt（Ⅲ）
Solution at 150 DEG C~170 DEG C, carry out refuxing esterification reaction, the water of oil water separator separation reaction generation, reaction is 4~6 small
Shi Hou, vacuum distillation remove removal xylene, and the acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two is made（Ⅳ）, its primary chemical
React and be：
It is further that the mol ratio of described n-dodecane dicarboxylic acids and tetrahydroxyethyl-ethylene diamine is 1 ﹕ 2~2.5.
Described catalyst is sulfuric acid and its metal ammonium salt or sulfamic acid and its metal salt, and its dosage is four ethoxy second
The 0.7%~1.5% of diamines quality.
A kind of acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two of the present invention and preparation method thereof, its feature and advantage
It is：Sufficient raw, cost are relatively low；Synthetic is a kind of acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two, is had
Multiple groups combined with metal, can play preferable anti-rust action；With multiple ethoxys, good water solubility；Synthetic is one
Kind dibasic acid esters, has lubricity；Operation is simple and easy, is adapted to industrialized production.
Embodiment
Embodiment 1
In the four-hole bottle equipped with agitating device, reflux condensate device and thermometer, 20 grams of water are added, add 41.5 gram four
AEEA, 20 grams of n-dodecane dicarboxylic acids are added portionwise, stirring reaction is produced after 1~2 hour at 50 DEG C~60 DEG C
The solution of n-dodecane dicarboxylic acids tetrahydroxyethyl-ethylene diamine salt, 100mL dimethylbenzene water entrainers are added, add 0.6 gram of catalyst
Sulfamic acid, it is heated at a temperature of 150 DEG C~170 DEG C, carries out refuxing esterification reaction, oil water separator separation reaction generation
Water, after reacting 4~6 hours, vacuum distillation removes removal xylene, and the acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two is made.
Embodiment 2
In the four-hole bottle equipped with agitating device, reflux condensate device and thermometer, 22 grams of water are added, add 53 gram of four hydroxyl
Ethylethylenediamine, 22.5 grams of n-dodecane dicarboxylic acids are added portionwise, stirring reaction is produced after 1~2 hour at 50 DEG C~60 DEG C
The solution of n-dodecane dicarboxylic acids tetrahydroxyethyl-ethylene diamine salt, 125mL dimethylbenzene water entrainers are added, add 0.7 gram of catalyst
Sulfamic acid potassium, it is heated at a temperature of 150 DEG C~170 DEG C, carries out refuxing esterification reaction, oil water separator separation reaction generation
Water, after reacting 4~6 hours, vacuum distillation removes removal xylene, and the acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two is made.
Embodiment 3
In the four-hole bottle equipped with agitating device, reflux condensate device and thermometer, 30 grams of water are added, add 64 gram of four hydroxyl
Ethylethylenediamine, 25 grams of n-dodecane dicarboxylic acids are added portionwise, stirring reaction is produced just after 1~2 hour at 50 DEG C~60 DEG C
The solution of dodecanedicarboxylic acid tetrahydroxyethyl-ethylene diamine salt, 150mL dimethylbenzene water entrainers are added, add 0.5 gram of catalyst sulphur
Sour iron ammonium, it is heated at a temperature of 150 DEG C~170 DEG C, carries out refuxing esterification reaction, the water of generation is reacted in oil water separator separation,
After reaction 4~6 hours, vacuum distillation removes removal xylene, and the acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two is made.
Described above, embodiment is only that the preferred embodiment of the present invention is described, not to the present invention's
Scope is defined, on the premise of the spirit of the technology of the present invention is not departed from, skill of this area engineers and technicians to the present invention
The various modifications and improvement that art scheme is made, it all should fall into the protection domain of claims of the present invention determination.
Claims (2)
1. a kind of preparation method of the acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two, it is characterized in that：Using a small amount of water to be molten
Agent, n-dodecane dicarboxylic acids carry out neutralization reaction, the ethoxy second two of generation n-dodecane dicarboxylic acids four with tetrahydroxyethyl-ethylene diamine
The solution of amine salt, under catalyst action, then using toluene as water entrainer, refuxing esterification reaction is carried out, is evaporated under reduced pressure and removes toluene,
Sebacate ethoxy tertiary amine compound is made, specifically comprises the steps of：
1) is using a small amount of water as solvent, n-dodecane dicarboxylic acids and tetrahydroxyethyl-ethylene diamine, the stirring reaction 1 at 50 DEG C~60 DEG C
~2 hours, produce the solution of n-dodecane dicarboxylic acids tetrahydroxyethyl-ethylene diamine salt, n-dodecane dicarboxylic acids tetrahydroxyethyl-ethylene diamine
The structural formula of salt is：
；
2) is using dimethylbenzene as water entrainer, under catalyst action, the solution of n-dodecane dicarboxylic acids tetrahydroxyethyl-ethylene diamine salt in
At 150 DEG C~170 DEG C, refuxing esterification reaction is carried out, the water of oil water separator separation reaction generation, after reacting 4~6 hours, is subtracted
Dimethylbenzene is distilled off in pressure, and the acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two is made, and the structural formula of its primary product is：
。
2. a kind of preparation method of the acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two according to claim 1, its
It is characterized in：Described n-dodecane dicarboxylic acids and the mol ratio of tetrahydroxyethyl-ethylene diamine are 1 ﹕ 2~2.5；Described catalyst is
Sulfuric acid and its metal ammonium salt or sulfamic acid and its metal salt, its dosage are the 0.7%~1.5% of tetrahydroxyethyl-ethylene diamine quality.
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| CN201310603807.XA CN104672095B (en) | 2013-11-26 | 2013-11-26 | A kind of acid esters multi-hydroxy ethyl ethylene diamine compound of n-dodecane two and preparation method thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2196451A1 (en) * | 2007-10-11 | 2010-06-16 | Takasago International Corporation | Acylation reaction of hydroxyl group |
| CN102002415A (en) * | 2009-09-02 | 2011-04-06 | 中国石油天然气股份有限公司 | Ash-free antirust additive for industrial lubricant and preparation method thereof |
| CN102199467A (en) * | 2011-04-06 | 2011-09-28 | 修建东 | Preparation method of Alpha-donamide aqueous antirust lubricant |
-
2013
- 2013-11-26 CN CN201310603807.XA patent/CN104672095B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2196451A1 (en) * | 2007-10-11 | 2010-06-16 | Takasago International Corporation | Acylation reaction of hydroxyl group |
| CN102002415A (en) * | 2009-09-02 | 2011-04-06 | 中国石油天然气股份有限公司 | Ash-free antirust additive for industrial lubricant and preparation method thereof |
| CN102199467A (en) * | 2011-04-06 | 2011-09-28 | 修建东 | Preparation method of Alpha-donamide aqueous antirust lubricant |
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Inventor after: Zhang Yu Inventor after: Sun Changhong Inventor after: Li Fude Inventor before: Xiu Jiandong |
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Effective date of registration: 20171214 Address after: 264006 Wuhan Avenue, Yantai Development Zone, Shandong Province, No. 19 Applicant after: Yantai Thinking Finechem Technology Co., Ltd. Address before: 264006 18-3-8, Fengtai District, Yantai Development Zone, Shandong, China Applicant before: Xiu Jiandong |
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